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Volumn 11, Issue 12, 2009, Pages 2639-2641

Direct and regioselective c-h alkenylation of tetrahydropyrido[1,2-a] pyrimidines

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; PALLADIUM; PYRIMIDINE DERIVATIVE;

EID: 67249094112     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900627q     Document Type: Article
Times cited : (71)

References (39)
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    • Alonso-Alija, C.; Michels, M.; Schirok, H.; Schlemmer, K.-H.; Dodd, S.; Fitzgerald, M.; Bell, J.; Gill, A. WO2003053967A1, 2003.
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    • Frohn, M. J.; Hong, F.-T.; Liu, L.; Lopez, P.; Siegmund, A. C.; Tadesse, S.; Tamayo, N. WO 2005/070932A2, 2005.
    • Frohn, M. J.; Hong, F.-T.; Liu, L.; Lopez, P.; Siegmund, A. C.; Tadesse, S.; Tamayo, N. WO 2005/070932A2, 2005.
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    • 0002591690 scopus 로고
    • For pioneering work in this field, see
    • For pioneering work in this field, see: Moritani, I.; Fujiwara, Y. Tetrahedron Lett. 1967, 1119.
    • (1967) Tetrahedron Lett , pp. 1119
    • Moritani, I.1    Fujiwara, Y.2
  • 11
    • 33947092471 scopus 로고    scopus 로고
    • For examples of Pd-mediated C-H activation and alkenylation of aryl and heteroaryl substrates, see: Trost, B. M, Godleski, S. A, Genet, J. P. J. Am. Chem. Soc. 1978, 100, 3930
    • For examples of Pd-mediated C-H activation and alkenylation of aryl and heteroaryl substrates, see: Trost, B. M.; Godleski, S. A.; Genet, J. P. J. Am. Chem. Soc. 1978, 100, 3930.
  • 31
    • 33644658464 scopus 로고    scopus 로고
    • For analogous regioselectivity studies associated with pyrroles and application to total synthesis, see
    • For analogous regioselectivity studies associated with pyrroles and application to total synthesis, see: Beck, E. M.; Grimster, N. P.; Hatley, R.; Gaunt, M. J. J. Am. Chem. Soc. 2006, 128. 2528.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 2528
    • Beck, E.M.1    Grimster, N.P.2    Hatley, R.3    Gaunt, M.J.4
  • 35
    • 50249118513 scopus 로고    scopus 로고
    • Various mechanistic possibilities exist for C - H activation with Pd(II). These most frequently link electrophilic aromatic substitution to electron-rich, π-excessive (hetero)arenes and, more recently, concerted metalation - deprotonation for simple and electron-deficient arenes. For a summary of mechanistic possibilities and leading references, see: Gorelsky, S. I.; Lapomte, D.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 10848.
    • Various mechanistic possibilities exist for C - H activation with Pd(II). These most frequently link electrophilic aromatic substitution to electron-rich, π-excessive (hetero)arenes and, more recently, concerted metalation - deprotonation for simple and electron-deficient arenes. For a summary of mechanistic possibilities and leading references, see: Gorelsky, S. I.; Lapomte, D.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 10848.
  • 36
    • 67249114918 scopus 로고    scopus 로고
    • (7) and C(9) regioisomers and C(7)/C(9) bishalogenation products: Cheng, D
    • Reaction of 2a with NCS or NBS gave mixtures of C Unpublished results
    • Reaction of 2a with NCS or NBS gave mixtures of C(7) and C(9) regioisomers and C(7)/C(9) bishalogenation products: Cheng, D. Unpublished results.
  • 37
    • 54849420705 scopus 로고    scopus 로고
    • The possibility that the C=O group directs palladation at C(7) has been rasied by a reviewer, and carbonyl directing effects have been recently reported: Giri, R.; Yu, J.-Q J. Am. Chem. Soc. 2008, 130, 14082.
    • The possibility that the C=O group directs palladation at C(7) has been rasied by a reviewer, and carbonyl directing effects have been recently reported: Giri, R.; Yu, J.-Q J. Am. Chem. Soc. 2008, 130, 14082.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.